By Jenn der Bentson

For many crossdressers, one of the most nerve-wracking moments in a relationship is sharing the fact that you crossdress. It’s a big step in trust and vulnerability, and it’s natural to feel both excitement and trepidation when your partner responds with curiosity and a desire to see you dressed up. This moment can be a turning point, filled with potential for deeper connection but also the possibility of misunderstanding or discomfort.

It starts with when you decide to tell your wife, or girlfriend, or boyfriend, just friend, or whomever in which you decided to confide that you crossdress.

They will want to see you dressed up.

It’s that simple.

If you are considering telling someone, anyone, or everyone, that you crossdress, be ready for this. sure, you can say no, but they are going to ask.

And there are going to need to be some things that you have thought through, considered, and be ready to deal with or answer as a result.

First might be the hardest. Are you willing to have someone, anyone, see you crossdressed?

This can be a hard first step, or it might be something you have been yearning to do for many years and just can’t wait to “let the cat out of the bag” shall we say. Either way, once it is done, it can’t be undone. You have to be ready for this. 

Do You “Show” Yourself Dressed Up?

This is a tough question.

Ok, so let’s say you decided to show yourself.

You are going to have to decide now. “How” do you show, if you have chosen to do so.

Do you show pictures or give a live dressed up demonstration?

Many crossdressers have rushed to dress up immediately and give an impromptu and ill prepared “fashion show” to the person they have in whom they have confided.

Don’t take pictures unless you are willing to have people see them. They can’t be “untaken”. If it goes badly, you have to be ready to have those pictured without your permission. Some crossdressers have even had these types of pictures used against them maliciously later.

These are hard questions, hard decisions, but I might have gotten slightly ahead of myself already. Let’s come back to the “why do they want to see you” dressed up.

The Natural Curiosity

When you reveal to your partner that you crossdress, one of the most common reactions is curiosity. This isn’t just about the clothes; it’s about seeing a new facet of you that they hadn’t encountered before. They might wonder:

• What do you look like?
• How do you feel when dressed?
• Is this an expression of who you are, or just something fun you enjoy?

These are all valid questions, and their curiosity often leads to the next step: they want to see you dressed up. For your partner, this is likely an attempt to understand and connect with this part of your identity. For you, however, it might feel like standing on the edge of a high dive.

The Challenges of Showing Your Partner

The idea of dressing up in front of your partner can be thrilling, but it’s also intimidating. You might worry about the judging you.

You might be asking, “What if they think you look silly or unattractive?”

Another questions hat arises frequently is whether your dressing will change dynamics between you and them.

“Will they see you differently? Will it alter the way they perceive your masculinity or your relationship?”

Crossdressing is deeply personal, and sharing it feels like baring your soul. Sharing your “en femme” form is a deeply vulnerable moment. It takes lots of courage on your part to do this.

Fears are valid, and it’s okay to acknowledge them. Remember, vulnerability is part of building intimacy, and your partner likely senses the courage it takes to share this part of yourself.

Your partner, on the other hand, might feel also hesitant for entirely different reasons. They may worry about, “What if they don’t know how to respond or feel conflicted?”

It might make them wonder, “Does this change their understanding of who you are?”

Or even a concern related to social norms. Even if they’re open-minded, they might grapple with preconceived notions or fears about what others might think. How will family feel? Friends? Or even strangers if you are out together.

This is a big moment for both of you, and the key to navigating it lies in open communication and mutual understanding.

Making the Moment Fun and Memorable

While this moment can feel heavy with emotion, it also has the potential to be made a fun and enjoyable, even  playful experience. Here are some ways to make it lighter and more fun:

Start Small – Ease into it by sharing pictures first or starting with subtle elements like a favorite accessory or makeup item. This can help break the ice and allow both of you to process the experience incrementally.

Involve Your Partner – Invite your partner to participate. Let them help you pick out an outfit, apply makeup, or style your hair. This can turn the experience into a bonding activity rather than a performance.

Set the Scene – Create a relaxed and positive environment. Play music, share a glass of wine, or laugh about the process together. By framing it as something enjoyable, you’ll both feel more at ease.

Embrace the Humor – There’s bound to be a funny moment or two, whether it’s fumbling with a zipper or experimenting with makeup. Lean into the humor and allow yourselves to laugh—it’s a great way to diffuse tension.

The Emotional Impact: What It Means for Both of You

Seeing you dressed up will likely evoke a range of emotions for your partner. They might feel curious, supportive, surprised, shocked, or hesitant. This is a side of you they’ve never seen before, and they’ll want to understand it better. In the best of cases, partners feel honored that you’ve trusted them with something so personal. Even if they were prepared, seeing you fully dressed might take some adjustment.

On your side, you’re likely to feel relieve, pride, nervousness, and even some freedom. Once the moment has passed, you’ll feel lighter for having shared this part of yourself. Assuming they are accepting, seeing their acceptance and support can boost your confidence. It’s normal to worry about how they’re processing everything. In the best of cases, a freedom is present that allows you to express yourself in ways that may have been stifled to this point.

The key is to remember that these feelings are part of the process. It’s a lot for both of you to take in, and it’s okay to have mixed emotions.

Communication: The Foundation of Acceptance

Moving past this moment to mutual acceptance requires clear, compassionate communication. 

Be honest about your feelings.

Share your fears, hopes, and what crossdressing means to you. Let your partner know that their acceptance matters deeply but that you’re also nervous. Vulnerability builds trust.

Give your partner space to ask questions, even if they’re unsure how to phrase them. Reassure them that curiosity is welcome and that you’re happy to provide clarity.

This isn’t a one-and-done conversation. Continue checking in with your partner about how they’re feeling and share your own updates. This ensures that both of you feel heard and understood.

Be ready for judgment

My wife said, “You look like your mom,” when she first saw me dressed up. There is lots of psychology that could probably be done with that comment, but it’s also genetics. We are byproducts of our parents, so I guess it wasn’t all that surprising either.

Your partner might need time to process everything, and that’s okay. Respect their pace, and don’t pressure them to engage more than they’re comfortable with.

Be Ready for Changing Emotions

Initial curiosity may be followed by indifference, annoyance, rejection, or all of the above and more.

Depending on your relationship with who you share your crossdressing, you have to understand they will have emotions and reactions also. If it is a significant other, these emotions can be complex and vary over time. A crossdressing partner undermines the understanding a partner may have of who that person is, who they want to be, or how they are attracted to them. Some partners work through this, some thrive with, what we may describe as “variety”, and some reject entirely the concept of a partner who is fluid in their gender expression.

The best advice I can give here is share early in a relationship any crossdressing desires or practices. I didn’t in some previous relationships, and as I got older in life it became something that I shared earlier in any dating efforts. In some cases it was accepted, in those that it wasn’t, it was a sign to both parties that this wasn’t the relationship for either of us. Its better to find that out early instead of digging deep into a relationship with hidden factors that WILL bubble up later and can become catastrophic.

Just because someone initially is intrigued by you sharing with them that you, or you showing them that you crossdress, doesn’t mean it will be as interesting for them long term either.

The curiosity may wear off.

That isn’t to say that they will be unaccepting of it, they may depending on their boundaries and your activity level, but it also just may be that the “thrill has worn off” for them. That initial intrigue may just be that, and for the lucky ones, their significant others or friends may just accept that this is a part of who you a person is and go with it. I guess this is probably what most of us would hope for, right?

Building a Stronger Connection

This experience, while challenging, can ultimately deepen your relationship. By showing your partner this vulnerable side of yourself, you’re inviting them to know you more fully. If approached with love and understanding, this moment can strengthen trust, enhance intimacy, and potentially promote growth. 

Sharing something so personal fosters a deeper bond. Seeing you in a new light can create a richer, more nuanced connection. Both of you will learn more about yourselves and each other, broadening your perspectives.

Embrace the Journey Together

Revealing your crossdressing to your partner and sharing the experience of dressing up for them is a significant step, filled with emotions on both sides. While it’s natural to feel nervous or hesitant, it’s also an opportunity for growth, connection, and joy.

Approach the moment with honesty, humor, and patience. Acknowledge the challenges, but don’t forget to celebrate the courage it takes for both of you to navigate this together. With communication, understanding, and mutual respect, this can be a stepping stone toward a deeper, more accepting relationship.

So take a deep breath, pick out your favorite outfit, and remember: this is just another chapter in your story—one that has the potential to be as beautiful and unique as you are.